There's more to the Dominican than beaches

Vitamin D-deprived leisurati tend to head to the Dominican Republic for its wallet-sparing package holidays and sun-glutted winters. But the island's disarmingly seductive capital, Santo Domingo, demands at least a day on the itinerary. The city's Zone Colonial is the cradle of colonialism (Columbus's men docked their armada here in 1498), and the place remains an 11-square-block twist of time-scarred streetlets and ancient ruins. Bougainvillea dribbles over wrought-iron balconies, pastel-washed 16th-century homes line cobblestoned laneways and petal-confettied Spanish courtyards have all the fevered romance of a Gabriel Garcia Marquez novel. But not everything is nostalgic of a grander, more opulent past: Lively cafes, fashionable restaurants and a tropical jubilance have escorted the area into the present tense. Here's a primer to this city of firsts:

Arrive in Santo Domingo and check in for the night at the Nicolas de Ovando hotel, the most luxurious and historic place to bid buenas noches. It is perched on Calle de las Damas (Street of the Ladies), the oldest paved street in the New World, which owes its moniker to Diego Columbus's wife: It was constructed so that she and her lady friends might promenade without fraying their frocks. The hotel's imposing, fortress-like main building dates to 1502, and was once the home of Nicolas de Ovando, the Spanish explorer and the DR's first governor. Considerably modernized, the hotel retains a languid Old World majesty, with its hot-coloured walls, lazy ceiling fans and arched passageways. Grab a bite at the on-site resto La Residence, a shaded orchid-bejewelled terrace framed by columns in the molten shades of sunset. The menu is a lusty tropical take on Med fare.

The next morning, kick-start your day with a memorably smooth espresso at La Cafetera Colonial. This petite espresso bar cached on narrow Calle el Conde feels like the Caribbean version of Paris's La Pigalle. The place has reportedly not changed since it opened in 1933, and was once the caffeinating ground for Spanish intellectuals and philosophers exiled to the DR under the Franco regime. Today, you'll find equally ancient-looking moustachioed regulars sitting barside, drinking espresso and arguing energetically about politics.

After breakfast, visit La Catedral Primada, which is, as its name states, supposedly the first cathedral in the New World. Its first stone was laid by Diego Columbus himself in 1514, and construction dragged on until 1540: the soaring Gothic, Roman and baroque pile invites a whiplash-inducing wander.

Next, head to the Fortaleza Ozama, a still-forbidding 16th-century fortress facing the mouth of the Rio Ozama that once safeguarded the city from pirates. Cannons still point menacingly to the river below. A panoramic view of the city repays a steep hike to the top.

For a leisurely alfresco lunch, try the Restaurant Conde de Penalba. It faces the Parque Colon: the pretty, tree-hemmed central plaza (so named for its bronze statue of Christopher Columbus) is to this city what San Marco is to Venice. The restaurant's sunny terrace claims the finest real estate for people-watching and languid cerveza-quaffing.

Right next door is the Boutique del Fumador, among the city's stogie capitals, and the fragrant factory for Caoba cigars (you can watch them being rolled). Wend your way through the neighbourhood's narrow sun-baked streets (stop to peer through wrought-iron gates into some private 16th-century gardened courtyards, decorated with stone fountains and giant flower pots) until you get to women's boutique Jenny Polanco on Calle Padre Billini. Every self-respecting Dominican fashionista claims some Polanco in her wardrobe. Find silk dresses in saturated col-ours, sparkly jewels and fetching hand-painted evening bags.

Repair to the hotel for a pool-side siesta, or a restorative cafe con leche. Overlooking the Rio Ozama, the pool and surrounding cafe is a voguish meeting ground for local deal-closers: businessmen in bespoke linen suits puff on Romeo and Juliet cigars and sip espresso, their silk ties flapping in the tropical breeze. (The way Toronto poses as New York on celluloid, Santo Domingo often moonlights as Havana.)

It's 7 p. m. Time for a pre-dinner mojito or margarita at the wood-panelled Cibao bar in the hotel. Then it's a quick trot to Meson de Bari for an epic Dominican feast. The resto, a restored colonial home with turquoise and lemon-yellow walls, is festive and familial, with recipes handed down through the generations. Order the cangrejo guisado (a fire-licked crab stew) or the empanadas lambi (oven-gilded pillows of conch and yucca).

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